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here's a hint, game over wise, double check on everyone to make sure you have a full plan.

 Fight wise you need to be pretty beefy and it still took a lot of attempts and RNG luck for me to finally win.

Yeah beeing beefy is kinda a part you need, and if you paid the homeless people and go back to arlene, that should have a scene on how to save arlene without seeing the don.